• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

氧化还原中性钯催化的C-H官能团化反应,以羧酸或酸酐作为容易获得的起始原料来形成异吲哚啉酮。

Redox-neutral palladium-catalyzed C-H functionalization to form isoindolinones with carboxylic acids or anhydrides as readily available starting materials.

作者信息

Liang Hong-Wen, Ding Wei, Jiang Kun, Shuai Li, Yuan Yi, Wei Ye, Chen Ying-Chun

机构信息

†College of Pharmacy, Third Military Medical University, Chongqing 400038, China.

‡State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, China.

出版信息

Org Lett. 2015 Jun 5;17(11):2764-7. doi: 10.1021/acs.orglett.5b01185. Epub 2015 May 15.

DOI:10.1021/acs.orglett.5b01185
PMID:25978091
Abstract

An operationally simple, Pd-catalyzed C-H functionalization is described for the synthesis of important and useful isoindolinones from readily available carboxamides and carboxylic acids or anhydrides. The reactions proceed efficiently with a broad range of substrates under redox-neutral reaction conditions and tolerate a diversity of functional groups. The mechanistic investigation suggests that the reactions involve C-H activation, nucleophilic addition, β-O elimination, and dehydration steps.

摘要

本文描述了一种操作简单的钯催化C-H官能化反应,用于从容易获得的羧酰胺和羧酸或酸酐合成重要且有用的异吲哚啉酮。该反应在氧化还原中性反应条件下能与多种底物高效进行,并能耐受多种官能团。机理研究表明,该反应涉及C-H活化、亲核加成、β-O消除和脱水步骤。

相似文献

1
Redox-neutral palladium-catalyzed C-H functionalization to form isoindolinones with carboxylic acids or anhydrides as readily available starting materials.氧化还原中性钯催化的C-H官能团化反应,以羧酸或酸酐作为容易获得的起始原料来形成异吲哚啉酮。
Org Lett. 2015 Jun 5;17(11):2764-7. doi: 10.1021/acs.orglett.5b01185. Epub 2015 May 15.
2
Pd-catalyzed stereoselective oxidation of methyl groups by inexpensive oxidants under mild conditions: a dual role for carboxylic anhydrides in catalytic C--H bond oxidation.钯催化下廉价氧化剂在温和条件下对甲基的立体选择性氧化:羧酸酐在催化碳氢键氧化中的双重作用
Angew Chem Int Ed Engl. 2005 Dec 1;44(45):7420-4. doi: 10.1002/anie.200502767.
3
Ligand-free palladium-catalyzed aerobic oxidative coupling of carboxylic anhydrides with arylboronic acids.无配体钯催化羧酸酐与芳基硼酸的有氧氧化偶联反应。
Chem Asian J. 2014 Sep;9(9):2402-6. doi: 10.1002/asia.201402314. Epub 2014 Jun 6.
4
β-Functionalization of carboxylic anhydrides with β-alkyl substituents through carbene organocatalysis.β-取代羧酸酐的β-位官能团化通过卡宾有机催化实现。
Angew Chem Int Ed Engl. 2014 Dec 1;53(49):13506-9. doi: 10.1002/anie.201408604. Epub 2014 Oct 5.
5
Selective synthesis of either isoindole- or isoindoline-1-carboxylic acid esters by Pd(0)-catalyzed enolate arylation.通过 Pd(0)催化的烯醇化物芳基化反应选择性合成异吲哚-1-羧酸酯或异吲哚啉-1-羧酸酯。
J Org Chem. 2010 Sep 17;75(18):6267-70. doi: 10.1021/jo101054j.
6
Chelation-assisted Pd-catalysed ortho-selective oxidative C-H/C-H cross-coupling of aromatic carboxylic acids with arenes and intramolecular Friedel-Crafts acylation: one-pot formation of fluorenones.螯合辅助的钯催化芳香羧酸与芳烃的邻位选择性氧化C-H/C-H交叉偶联及分子内傅克酰基化反应:芴酮的一锅法合成
Chem Commun (Camb). 2016 Mar 4;52(18):3635-8. doi: 10.1039/c6cc00103c.
7
Phosphine-free cross-coupling reaction of arylboronic acids with carboxylic anhydrides or acyl chlorides in aqueous media.芳基硼酸与羧酸酐或酰氯在水介质中的无膦交叉偶联反应。
J Org Chem. 2006 Jul 21;71(15):5725-31. doi: 10.1021/jo060749d.
8
Integrated catalytic C-H transformations for one-pot synthesis of 1-arylisoindoles from isoindolines via palladium-catalyzed dehydrogenation followed by C-H arylation.通过钯催化脱氢和 C-H 芳基化,从异吲哚啉一锅合成 1-芳基异吲哚的集成催化 C-H 转化。
Org Lett. 2011 Mar 4;13(5):1238-41. doi: 10.1021/ol2001232. Epub 2011 Jan 28.
9
Palladium-catalyzed decarboxylative coupling of isatoic anhydrides with arylboronic acids.钯催化的异氰酸酐与芳基硼酸的脱羧偶联反应。
Org Lett. 2011 Nov 18;13(22):6114-7. doi: 10.1021/ol202609a. Epub 2011 Oct 20.
10
A general palladium-catalyzed carbonylative synthesis of 2-alkylbenzoxazinones from 2-bromoanilines and acid anhydrides.一种通用的钯催化的 2-溴苯胺和酸酐羰基化合成 2-烷基苯并恶嗪酮的方法。
Chemistry. 2012 Oct 1;18(40):12599-602. doi: 10.1002/chem.201202142. Epub 2012 Sep 3.

引用本文的文献

1
Copper-Catalyzed Asymmetric Hydroboration Reaction of Novel Methylene Isoindolinone Compounds through Microwave Irradiation and Their Antileishmanial and Antitoxoplasma Activities.新型亚甲基异吲哚啉酮化合物的铜催化不对称硼氢化反应:微波辐射及其抗利什曼原虫和抗弓形虫活性
ACS Omega. 2023 Jun 9;8(25):23067-23077. doi: 10.1021/acsomega.3c02362. eCollection 2023 Jun 27.
2
Nickel(ii)-catalyzed tandem C(sp)-H bond activation and annulation of arenes with -dibromoalkenes.镍(II)催化芳烃与α,α'-二溴烯烃的串联C(sp)-H键活化和环化反应
RSC Adv. 2018 Aug 13;8(50):28668-28675. doi: 10.1039/c8ra03278e. eCollection 2018 Aug 7.
3
CsCO-promoted defluorination and functionalization of α-CF carbonyl compounds in the presence of -, -, and/or -nucleophiles.
在存在 -、- 和/或 - 亲核试剂的情况下,CsCO促进α-CF羰基化合物的脱氟和官能化反应。
RSC Adv. 2018 Apr 30;8(29):16019-16023. doi: 10.1039/c8ra02353k. eCollection 2018 Apr 27.
4
Isoindolinone Synthesis via One-Pot Type Transition Metal Catalyzed C-C Bond Forming Reactions.通过一锅式过渡金属催化的C-C键形成反应合成异吲哚啉酮
Chemistry. 2021 Mar 22;27(17):5344-5378. doi: 10.1002/chem.202004375. Epub 2021 Feb 2.
5
A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.指导基团在金属催化 C-H 官能化化学中的应用综述。
Chem Soc Rev. 2018 Aug 28;47(17):6603-6743. doi: 10.1039/c8cs00201k.